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Article

Solvent-Controlled Self-Assembled Oligopyrrolic Receptor †

by
Fei Wang
1,
Kejiang Liang
1,
Mads Christian Larsen
2,
Steffen Bähring
2,*,
Masatoshi Ishida
3,*,
Hiroyuki Furuta
3,* and
Atanu Jana
4,*
1
Center for Supramolecular Chemistry and Catalysis, Department of Chemistry, Shanghai University, No. 333 Nanchen Road, Baoshan District, Shanghai 200444, China
2
Department of Physics, Chemistry and Pharmacy, University of Southern Denmark, Campusvej 55, 5230 Odense, Denmark
3
Center for Molecular Systems, Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, Fukuoka 819-0395, Japan
4
Department of Chemistry, Gandhi Institute of Technology and Management (GITAM), NH 207, Nagadenehalli, Doddaballapur Taluk, Bengaluru 561203, India
*
Authors to whom correspondence should be addressed.
†
Dedicated to our mentor Professor Jonathan L. Sessler on the occasion of his 65th birthday.
Molecules 2021, 26(6), 1771; https://doi.org/10.3390/molecules26061771
Submission received: 31 January 2021 / Revised: 13 March 2021 / Accepted: 18 March 2021 / Published: 22 March 2021
(This article belongs to the Special Issue Supramolecular Anion Binding and Molecular Recognition)
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Abstract

We report a fully organic pyridine-tetrapyrrolic U-shaped acyclic receptor 10, which prefers a supramolecular pseudo-macrocyclic dimeric structure (10)2 in a less polar, non-coordinating solvent (e.g., CHCl3). Conversely, when it is crystalized from a polar, coordinating solvent (e.g., N,N-dimethylformamide, DMF), it exhibited an infinite supramolecular one-dimensional (1D) “zig-zag” polymeric chain, as inferred from the single-crystal X-ray structures. This supramolecular system acts as a potential receptor for strong acids, e.g., p-toluenesulfonic acid (PTSA), methane sulfonic acid (MSA), H2SO4, HNO3, and HCl, with a prominent colorimetric response from pale yellow to deep red. The receptor can easily be recovered from the organic solution of the host–guest complex by simple aqueous washing. It was observed that relatively stronger acids with pKa < −1.92 in water were able to interact with the receptor, as inferred from 1H NMR titration in tetrahydrofuran-d8 (THF-d8) and ultraviolet–visible (UV–vis) spectroscopic titrations in anhydrous THF at 298 K. Therefore, this new dynamic supramolecular receptor system may have potentiality in materials science research.
Keywords: supramolecular receptor; host–guest chemistry; colorimetric acid-sensing; oligopyrrole supramolecular receptor; host–guest chemistry; colorimetric acid-sensing; oligopyrrole
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MDPI and ACS Style

Wang, F.; Liang, K.; Larsen, M.C.; Bähring, S.; Ishida, M.; Furuta, H.; Jana, A. Solvent-Controlled Self-Assembled Oligopyrrolic Receptor. Molecules 2021, 26, 1771. https://doi.org/10.3390/molecules26061771

AMA Style

Wang F, Liang K, Larsen MC, Bähring S, Ishida M, Furuta H, Jana A. Solvent-Controlled Self-Assembled Oligopyrrolic Receptor. Molecules. 2021; 26(6):1771. https://doi.org/10.3390/molecules26061771

Chicago/Turabian Style

Wang, Fei, Kejiang Liang, Mads Christian Larsen, Steffen Bähring, Masatoshi Ishida, Hiroyuki Furuta, and Atanu Jana. 2021. "Solvent-Controlled Self-Assembled Oligopyrrolic Receptor" Molecules 26, no. 6: 1771. https://doi.org/10.3390/molecules26061771

APA Style

Wang, F., Liang, K., Larsen, M. C., Bähring, S., Ishida, M., Furuta, H., & Jana, A. (2021). Solvent-Controlled Self-Assembled Oligopyrrolic Receptor. Molecules, 26(6), 1771. https://doi.org/10.3390/molecules26061771

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